Triethylamine → HCID 54536538, compound

HRID 620405Notes

Reaction equation

HRID 620405 reaction equation
C(Cl)(=O)C(C)(C)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15](O)=[O:16].C(N(CC)CC)C.Cl.[CH3:31][NH:32][OH:33]>CN(C)C=O.C(OCC)(=O)C.C(OCC)C>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15]([N:32]([CH3:31])[OH:33])=[O:16]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 168483',4'-Dimethoxycinnamic acidHCID 62493Pivaloyl chlorideHCID 77906N-methylhydroxylamine hydrochloride

Product 1

HCID 54536538HCID 54536538, compoundYield 42.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Pivaloyl chloride (23.5 g, 195 mmol) was added dropwise to a stirred solution of 3,4-dimethoxycinnamic acid (40 g, 192 mmol) and triethylamine (54.4 ml, 390 mmol) in N,N-dimethylformamide (600 ml) at -30° C. To the resulting mixture was added a solution of N-methylhydroxylamine hydrochloride (15.9 g, 190 mmol) in N,N-dimethylformamide (50 ml). The mixture was allowed to warm slowly to room temperature. Ethyl ether (600 ml) was added, and the precipitated triethylamine hydrochloride filtered off. The filtrate was concentrated in vacuo to leave a yellow oil, which was dissolved in 400 ml ethyl acetate. Additional triethylamine hydrochloride was removed by filtration, and the filtrate seeded and allowed to stand at room temperature overnight. The precipitated product was collected by filtration, dried in vacuo, and recrystallized from methanol-water to provide 19.0 g of the named compound as a white powder, mp 149.5°-150.5° C.

Workup

  1. filtrationthe precipitated triethylamine hydrochloride filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto leave a yellow oil, which
  4. customAdditional triethylamine hydrochloride was removed by filtration
  5. filtrationThe precipitated product was collected by filtration
  6. customdried in vacuo
  7. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-3872f218796d4ffe9eb5463b3b534002
Source dataset
uspto-grants-1989_04
Patent number
US04820828

Reaction notes

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